What Keeps Entrepreneurs Up At Night

As an active member of the startup scene for the past several years, I’ve had the privilege of working with and watching a handful of what I’d consider to be some of the most exceptional entrepreneurs of our time. Innovative, talented and respectable people that seem to know exactly what they’re doing and where they’re going. How does one get to that place? How do they manage to not only hold it together under all of the pressure and stress, but to excel and to lead in the midst of it all?

Growing up, I held a similar notion that my leaders always had some sort of plan. Whether it was my little league coach who had a very precise reason for running each exercise or drill, or my camp counselor who put an incredible amount of thought into every activity he planned, all that were given any sort of leadership role had a very special set of gifts.

When I became a camp counselor myself, at least 80% of the things that I came up with were either completely on the fly or created by the camp itself. You could say I was unprepared almost all of the time. And my campers saw it, right? Surely they knew that I didn’t size up to my counselor predecessors.

It was one of my younger campers that taught me the most important lesson that I’ve learned in life so far. The sun was setting on Orcas Island and my campers and I had just sat down for dinner. Just prior to mealtime, the camp director made an announcement. “Before your table can get up for dessert, each of you must write a postcard home to your parents.”

As I collected postcards from each of my kids to hand over to the director, I couldn’t help but peek at the one on top. It only took two sentences for my camper to rock my world. “My camp counselor’s name is Chet and he is just like Dad! I’m having the best summer ever!” My world came crashing down around me. But wait, if he thinks that I’m the best counselor ever and I thought the same of my camp counselor… could my counselor have been just as unprepared and scared as I?

In short, hell yes. Nobody has the golden plan and that’s one of the fews things that I’m certain of. Kabir Shahani of Seattle startup Appature says of building a startup, “Startups are 95% luck, 4% timing and 1% hard work.” This was uplifting to me, and I’d like to move some things around in relating to life: “Life is 95% get off your ass and do something, 4% who knows and 1% I’m so talented everything is happening for me.”

Now that I’ve nearly finished this article, I’m asking myself, “why would any dignified reader care about what I have to say? At this point my name is most likely unrecognizable, I’m only 25 and I haven’t done anything that amazing.” Although I sincerely hope these weren’t the questions you were asking, I want to reinforce the things that I’ve said above. To do that, I reached out to some of the most successful entrepreneurs around and asked them, “If this topic hits home, I’d love a quote on something that you struggle with.” I was blown away by the response, and I think you will be too.

T.A. McCann
“As a CEO, you are supposed to have answers, but you know inherently that there are smarter people in almost every area around the table. I feel the need to offer an opinion or an answer, and will do so with conviction, but I fear the team will see me as a fraud or at minimum, disingenuous.”

Amy Balliett (Co-Founder Killer Infographics)
Every night at 3am, I wake up in a panic about my company and start making lists. It doesn’t matter what night of the week it is, there’s always a list of things I forgot to do, things I need to redo, and things I have yet to do. I’m under the constant belief that, if these things don’t get done then my business will stall and my employees will bare the brunt of it. The problem is that the longer I run my business, the longer the lists get. A successful day is when I can accomplish just two things on the list, but those will inevitably create another four tasks that I didn’t think of before.”

Rand Fishkin (Co-Founder/CEO Moz.com)
“I struggle constantly with feeling like an underachiever. It doesn’t matter how much Moz grows or how successful we are, at least a few times a week I’m wracked with feelings of guilt (for not accomplishing more), insecurity (what if all our customers leave tomorrow?), and inadequacy (someone else could do this job better than me). When I was a kid my Dad would describe me to people as being ‘high potential, low achiever.’ I don’t think I ever outgrew the fear that he was right.”

So how does one get to a place where they can manage under the pressure and hold everything together all the time? The truth is, they don’t. A wise man once said to me, “every morning I wake up and expect to see a 23 year old boy staring back at me, but instead see a weathered and much grayer 50-something year old man.” Our bones may ache and our hair may gray, but at the end of the day we’re all young at heart. None of us know exactly what we’re doing or where we’re going, and that’s okay. As long as we realize that we’re not alone and that we are human — just like the founders and CEO’s from before us — we’ll be just fine.